diff --git a/espanso/src/cli/worker/engine/matcher/rolling.rs b/espanso/src/cli/worker/engine/matcher/rolling.rs
index dfe1fc9..b0e6b90 100644
--- a/espanso/src/cli/worker/engine/matcher/rolling.rs
+++ b/espanso/src/cli/worker/engine/matcher/rolling.rs
@@ -17,7 +17,10 @@
  * along with espanso.  If not, see <https://www.gnu.org/licenses/>.
  */
 
-use espanso_match::rolling::{matcher::RollingMatcher, RollingMatch};
+use espanso_match::rolling::{
+  matcher::{RollingMatcher, RollingMatcherOptions},
+  RollingMatch,
+};
 
 use crate::engine::{
   event::keyboard::Key,
@@ -32,13 +35,30 @@ pub struct RollingMatcherAdapter {
 
 impl RollingMatcherAdapter {
   pub fn new(matches: &[RollingMatch<i32>]) -> Self {
-    let matcher = RollingMatcher::new(matches, Default::default());
+    // TODO: load them from config
+
+    let matcher = RollingMatcher::new(
+      matches,
+      RollingMatcherOptions {
+        char_word_separators: vec![
+          " ".to_string(),
+          ",".to_string(),
+          ".".to_string(),
+          "?".to_string(),
+          "!".to_string(),
+          "\r".to_string(),
+          "\n".to_string(),
+          (22u8 as char).to_string(),
+        ],
+        key_word_separators: vec![],
+      },
+    );
 
     Self { matcher }
   }
 }
 
-impl <'a> Matcher<'a, MatcherState<'a>> for RollingMatcherAdapter {
+impl<'a> Matcher<'a, MatcherState<'a>> for RollingMatcherAdapter {
   fn process(
     &'a self,
     prev_state: Option<&MatcherState<'a>>,
@@ -80,8 +100,10 @@ impl From<espanso_match::MatchResult<i32>> for MatchResult {
   fn from(result: espanso_match::MatchResult<i32>) -> Self {
     Self {
       id: result.id,
-      trigger: result.trigger, 
-      args: result.vars, 
+      trigger: result.trigger,
+      left_separator: result.left_separator,
+      right_separator: result.right_separator,
+      args: result.vars,
     }
   }
 }
diff --git a/espanso/src/cli/worker/engine/multiplex.rs b/espanso/src/cli/worker/engine/multiplex.rs
index 6961d72..41a4d8d 100644
--- a/espanso/src/cli/worker/engine/multiplex.rs
+++ b/espanso/src/cli/worker/engine/multiplex.rs
@@ -21,10 +21,7 @@ use std::collections::HashMap;
 
 use espanso_config::matches::{Match, MatchEffect};
 
-use crate::engine::{
-  event::{render::RenderingRequestedEvent, Event},
-  process::Multiplexer,
-};
+use crate::engine::{event::{Event, matches::DetectedMatch, render::RenderingRequestedEvent}, process::Multiplexer};
 
 pub trait MatchProvider<'a> {
   fn get(&self, match_id: i32) -> Option<&'a Match>;
@@ -41,14 +38,16 @@ impl<'a> MultiplexAdapter<'a> {
 }
 
 impl<'a> Multiplexer for MultiplexAdapter<'a> {
-  fn convert(&self, match_id: i32, trigger: Option<String>, trigger_args: HashMap<String, String>) -> Option<Event> {
-    let m = self.provider.get(match_id)?;
+  fn convert(&self, detected_match: DetectedMatch) -> Option<Event> {
+    let m = self.provider.get(detected_match.id)?;
 
     match &m.effect {
       MatchEffect::Text(_) => Some(Event::RenderingRequested(RenderingRequestedEvent {
-        match_id,
-        trigger,
-        trigger_args,
+        match_id: detected_match.id,
+        trigger: detected_match.trigger,
+        left_separator: detected_match.left_separator,
+        right_separator: detected_match.right_separator,
+        trigger_args: detected_match.args,
       })),
       // TODO: think about rich text and image
       MatchEffect::None => None,
diff --git a/espanso/src/engine/event/effect.rs b/espanso/src/engine/event/effect.rs
index 8c8c7a6..501ebc8 100644
--- a/espanso/src/engine/event/effect.rs
+++ b/espanso/src/engine/event/effect.rs
@@ -20,6 +20,7 @@
 #[derive(Debug, Clone, PartialEq)]
 pub struct TriggerCompensationEvent {
   pub trigger: String,
+  pub left_separator: Option<String>,
 }
 
 #[derive(Debug, Clone, PartialEq)]
diff --git a/espanso/src/engine/event/matches.rs b/espanso/src/engine/event/matches.rs
index 6c68fd8..af1976c 100644
--- a/espanso/src/engine/event/matches.rs
+++ b/espanso/src/engine/event/matches.rs
@@ -28,6 +28,8 @@ pub struct MatchesDetectedEvent {
 pub struct DetectedMatch {
   pub id: i32,
   pub trigger: Option<String>,
+  pub left_separator: Option<String>,
+  pub right_separator: Option<String>,
   pub args: HashMap<String, String>,
 }
 
diff --git a/espanso/src/engine/event/render.rs b/espanso/src/engine/event/render.rs
index 23e2573..09a6a22 100644
--- a/espanso/src/engine/event/render.rs
+++ b/espanso/src/engine/event/render.rs
@@ -23,6 +23,8 @@ use std::collections::HashMap;
 pub struct RenderingRequestedEvent {
   pub match_id: i32,
   pub trigger: Option<String>,
+  pub left_separator: Option<String>,
+  pub right_separator: Option<String>,
   pub trigger_args: HashMap<String, String>,
 }
 
diff --git a/espanso/src/engine/process/middleware/action.rs b/espanso/src/engine/process/middleware/action.rs
index e6ef859..4c99871 100644
--- a/espanso/src/engine/process/middleware/action.rs
+++ b/espanso/src/engine/process/middleware/action.rs
@@ -61,11 +61,18 @@ impl<'a> Middleware for ActionMiddleware<'a> {
             .collect(),
         })
       }
-      Event::TriggerCompensation(m_event) => Event::KeySequenceInject(KeySequenceInjectRequest {
-        keys: (0..m_event.trigger.chars().count())
-          .map(|_| Key::Backspace)
-          .collect(),
-      }),
+      Event::TriggerCompensation(m_event) => {
+        let mut backspace_count = m_event.trigger.chars().count();
+
+        // We want to preserve the left separator if present
+        if let Some(left_separator) = &m_event.left_separator {
+          backspace_count -= left_separator.chars().count();
+        }
+
+        Event::KeySequenceInject(KeySequenceInjectRequest {
+          keys: (0..backspace_count).map(|_| Key::Backspace).collect(),
+        })
+      }
       _ => event,
     }
 
diff --git a/espanso/src/engine/process/middleware/cause.rs b/espanso/src/engine/process/middleware/cause.rs
index cf65731..f4ff571 100644
--- a/espanso/src/engine/process/middleware/cause.rs
+++ b/espanso/src/engine/process/middleware/cause.rs
@@ -53,6 +53,7 @@ impl Middleware for CauseCompensateMiddleware {
         // Before the event, place a trigger compensation
         return Event::TriggerCompensation(TriggerCompensationEvent {
           trigger: trigger.clone(),
+          left_separator: m_event.chosen.left_separator.clone(),
         });
       } else {
         return compensated_event;
diff --git a/espanso/src/engine/process/middleware/matcher.rs b/espanso/src/engine/process/middleware/matcher.rs
index 0923754..827c6e7 100644
--- a/espanso/src/engine/process/middleware/matcher.rs
+++ b/espanso/src/engine/process/middleware/matcher.rs
@@ -105,6 +105,8 @@ impl<'a, State> Middleware for MatcherMiddleware<'a, State> {
               .map(|result| DetectedMatch {
                 id: result.id,
                 trigger: Some(result.trigger),
+                right_separator: result.right_separator,
+                left_separator: result.left_separator,
                 args: result.args,
               })
               .collect(),
diff --git a/espanso/src/engine/process/middleware/multiplex.rs b/espanso/src/engine/process/middleware/multiplex.rs
index ff9d9cc..49391a4 100644
--- a/espanso/src/engine/process/middleware/multiplex.rs
+++ b/espanso/src/engine/process/middleware/multiplex.rs
@@ -39,7 +39,7 @@ impl<'a> Middleware for MultiplexMiddleware<'a> {
 
   fn next(&self, event: Event, _: &mut dyn FnMut(Event)) -> Event {
     if let Event::CauseCompensatedMatch(m_event) = event {
-      return match self.multiplexer.convert(m_event.m.id, m_event.m.trigger, m_event.m.args) {
+      return match self.multiplexer.convert(m_event.m) {
         Some(event) => event,
         None => {
           error!("match multiplexing failed");
diff --git a/espanso/src/engine/process/middleware/render.rs b/espanso/src/engine/process/middleware/render.rs
index ccbb889..1040ea4 100644
--- a/espanso/src/engine/process/middleware/render.rs
+++ b/espanso/src/engine/process/middleware/render.rs
@@ -48,6 +48,12 @@ impl<'a> Middleware for RenderMiddleware<'a> {
     if let Event::RenderingRequested(m_event) = event {
       match self.renderer.render(m_event.match_id, m_event.trigger_args) {
         Ok(body) => {
+          let body = if let Some(right_separator) = m_event.right_separator {
+            format!("{}{}", body, right_separator)
+          } else {
+            body
+          };
+
           return Event::Rendered(RenderedEvent {
             match_id: m_event.match_id,
             body,
diff --git a/espanso/src/engine/process/mod.rs b/espanso/src/engine/process/mod.rs
index e4937d3..0b91b2a 100644
--- a/espanso/src/engine/process/mod.rs
+++ b/espanso/src/engine/process/mod.rs
@@ -17,7 +17,7 @@
  * along with espanso.  If not, see <https://www.gnu.org/licenses/>.
  */
 
-use super::{event::keyboard::Key, Event};
+use super::{Event, event::{keyboard::Key, matches::DetectedMatch}};
 use anyhow::Result;
 use std::collections::HashMap;
 use thiserror::Error;
@@ -56,6 +56,8 @@ pub enum MatcherEvent {
 pub struct MatchResult {
   pub id: i32,
   pub trigger: String,
+  pub left_separator: Option<String>,
+  pub right_separator: Option<String>,
   pub args: HashMap<String, String>,
 }
 
@@ -70,9 +72,7 @@ pub trait MatchSelector {
 pub trait Multiplexer {
   fn convert(
     &self,
-    match_id: i32,
-    trigger: Option<String>,
-    trigger_args: HashMap<String, String>,
+    m: DetectedMatch,
   ) -> Option<Event>;
 }